U.S. patent number 6,090,750 [Application Number 08/814,946] was granted by the patent office on 2000-07-18 for herbicidal combinations.
This patent grant is currently assigned to Novartis AG. Invention is credited to Luke L. Bozeman, Reynold Chollet.
United States Patent |
6,090,750 |
Chollet , et al. |
July 18, 2000 |
Herbicidal combinations
Abstract
The invention discloses a novel method for reducing
phytotoxicity of Dicamba to crop plants, which comprises
co-applying to the crop plants or to the locus thereof a
phytotoxicity reducing effective amount of a quinolinyloxy alkanoic
acid derivative together with a herbicidally effective amount of
Dicamba and salt forms thereof.
Inventors: |
Chollet; Reynold (Bottmingen,
CH), Bozeman; Luke L. (Jupiter, FL) |
Assignee: |
Novartis AG (Basel,
CH)
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Family
ID: |
26308921 |
Appl.
No.: |
08/814,946 |
Filed: |
March 10, 1997 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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735289 |
Oct 22, 1996 |
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Foreign Application Priority Data
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Mar 13, 1996 [GB] |
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9605252 |
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Current U.S.
Class: |
504/105; 504/130;
504/138; 504/144; 504/324 |
Current CPC
Class: |
A01N
37/40 (20130101); A01N 47/34 (20130101); A01N
37/40 (20130101); A01N 47/34 (20130101); A01N
43/42 (20130101); A01N 25/32 (20130101); A01N
47/34 (20130101); A01N 25/32 (20130101); A01N
37/40 (20130101); A01N 2300/00 (20130101); A01N
47/34 (20130101); A01N 2300/00 (20130101) |
Current International
Class: |
A01N
37/40 (20060101); A01N 37/36 (20060101); A01N
47/28 (20060101); A01N 47/34 (20060101); A01N
025/32 (); A01N 037/10 (); A01N 043/40 (); A01N
043/42 () |
Field of
Search: |
;504/105,130,138,144,324
;71/DIG.1 |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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354 201 |
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Feb 1990 |
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EP |
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646315 |
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Apr 1995 |
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EP |
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2129109 |
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Jan 1973 |
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DE |
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1362886 |
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Aug 1974 |
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GB |
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9424858 |
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Nov 1994 |
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WO |
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Other References
EPO Search Report, Application No. EP 97102604 (May 1997). .
Gauvrit,et al. Oils for Weed Control: Uses and Mode of Action,
1993, Pesticide Sci., 37, 147-153..
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Primary Examiner: Pak; John
Attorney, Agent or Firm: Morris; Michael P. Peabody, III;
John D. Teoli, Jr.; William A.
Parent Case Text
This application is a continuation of Ser. No. 08/735,289, filed on
Oct. 22, 1996, now abandoned.
Claims
What is claimed is:
1. A method for reducing phytotoxicity of Dicamba to crop plants,
which comprises co-applying to the crop plants or to the locus
thereof a phytotoxicity reducing effective amount of a
quinolinyloxy alkanoic acid derivative together with a herbicidally
effective amount of Dicamba of formula I ##STR4## and salt forms
thereof; and wherein said quinolinyloxy alkanoic acid derivative is
selected from the compounds of formula II ##STR5## wherein R.sub.1
is hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein said Dicamba is applied in an amount from 50 to 2000 g/ha;
and
wherein said quinolinyloxy alkanoic acid derivative is applied in
an amount from 10 to 2000 g/ha.
2. A method according to claim 1 wherein the quinolinyloxy alkanoic
acid derivative is Cloquintocet-mexyl.
3. A method according to claim 1 wherein additionally a compound of
formula III ##STR6## wherein M is hydrogen, or a salt forming
moiety, and X and Y represent independent hydrogen, fluorine or
chlorine, is applied with the combination of compounds of formulae
I and II.
4. A method according to claim 3, wherein the compound of formula
III is Diflufenzopyr.
5. A method of selectively controlling unwanted plant growth in
monocotyledoneous crops which comprises co-application to the locus
of said unwanted plant growth an herbicidally effective amount of
Dicamba and salt forms thereof, and a phytotoxicity reducing
effective amount of a quinolinyloxy alkanoic acid derivative;
and
wherein said quinolinyloxy alkanoic acid derivative is selected
from the compounds of formula II
##STR7## wherein R.sub.1 is hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein said Dicamba is applied in an amount from 50 to 2000 g/ha;
and
wherein said quinolinyloxy alkanoic acid derivative is applied in
an amount from 10 to 2000 g/ha.
6. A method according to claim 5 wherein the quinolinyloxy alkanoic
acid derivative is Cloquintocet-mexyl.
7. A method according to claim 5 wherein additionally a compound of
formula III ##STR8## wherein M is hydrogen, or a salt forming
moiety, and X and Y represent independent hydrogen, fluorine or
chlorine, is applied with the combination of said dicamba and said
quinolinyloxy alkanoic acid derivative.
8. A method according to claim 7, wherein the compound of formula
III is Diflufenzopyr.
9. A herbicidal composition comprising a herbicidally effective
aggregate amount of dicamba and salt forms thereof, and of
phytotoxicity reducing effective amount of a quinolinyloxy alkanoic
acid derivative; and
wherein said quinolinyloxy alkanoic acid derivative is selected
from the compounds of formula II ##STR9## wherein R.sub.1 is
hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein the weight ratio of said Dicamba to said quinolinyloxy
alkanoic acid derivative is in the range of 1:40 to 200:1.
10. A herbicidal composition according to claim 9 wherein the
quinolinyloxy alkanoic acid derivative is Cloquintocet-mexyl.
11. A herbicidal composition comprising a herbicidally effective
aggregate amount of Dicamba and salt forms thereof, and of a
semicarbazone compound and of phytotoxicity reducing effective
amount of a quinolinyloxy alkanoic acid derivative; and
wherein said quinolinyloxy alkanoic acid derivative is selected
from the compounds of formula II ##STR10## wherein R.sub.1 is
hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein the weight ratio of said Dicamba to said quinolinyloxy
alkanoic acid derivative is in the range of 1:40 to 200:1, and the
weight ratio of said Dicamba to the said semicarbazone compound is
in the range of 1:100 to 1000:1.
12. A herbicidal composition according to claim 11 wherein the
semicarbazone is selected from the compounds of formula III
##STR11## wherein M is hydrogen, or a salt forming moiety, and X
and Y represent independent hydrogen, fluorine or chlorine.
13. A herbicidal composition according to claim 11 wherein the
quinolinyloxy alkanoic acid derivative is Cloquintocet-mexyl.
14. A herbicidal composition according to claim 11 wherein the
semicarbazone compound is Diflufenzopyr.
15. A method for reducing phytotoxicity of Dicamba to crop plants,
which comprises co-applying to the crop plants or to the locus
thereof a phytotoxicity reducing effective amount of a
quinolinyloxy alkanoic acid derivative together with a herbicidally
effective amount of Dicamba of formula I ##STR12## and salt forms
thereof; and wherein said quinolinyloxy alkanoic acid derivative is
selected from the compounds of formula II ##STR13## wherein R.sub.1
is hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein said quinolinyloxy alkanoic acid derivative is applied as a
seed dressing; and
wherein the application rate of said quinolinyloxy alkanoic acid
derivative is from 1.0 to 1000 g per 100 kg of seeds.
16. A method of selectively controlling unwanted plant growth in
monocotyledoneous crops which comprises co-application to the locus
of said unwanted plant growth an herbicidally effective amount of
Dicamba and salt forms thereof and a phytotoxicity reducing
effective amount of a quinolinyloxy alkanoic acid derivative;
and
wherein said quinolinyloxy alkanoic acid derivative is selected
from the compounds of formula II ##STR14## wherein R.sub.1 is
hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alkyl, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl; and
wherein said quinolinyloxy alkanoic acid derivative is applied as a
seed dressing, and
wherein the application rate of said quinolinyloxy alkanoic acid
derivative is from 1.0 to 1000 g per 100 kg of seeds.
Description
The present invention relates to a method of controlling undesired
plant growth employing co-application of Dicamba and a
quinolinyloxy alkanoic acid derivative. The invention further
concerns herbicidal compositions comprising Dicamba and a
quinolinyloxy alkanoic acid derivative.
The method of the present invention in particular provides reduced
phytotoxicity for monocotylodoneous crop plants, such as maize,
sorghum, turf, and cereals, against the damaging effect of Dicamba.
Likewise the herbicidal compositions according to present invention
comprising Dicamba as herbicidal agent have an improved tolerance
in the treated crops.
Dicamba is a well-known pre- and post-emergence herbicide for the
selective control of annual and perennial broad-leaved weeds and
brush species in cereals, maize, sorghum, sugar cane, asparagus,
perennial seed grasses, turf, pastures, rangeland, and non-crop
land. Dicamba is preferably applied post-emergence. Dicamba
(hereafter Compound I) designates the compound of formula I
##STR1## and salt forms thereof. Dicamba is commercially available
under the trademark BANVEL.RTM., and is in practice employed as
herbicide in form of the free acid, the sodium salt, potassium
salt, dimethylammonium-salt (DMA salt), or diglycolamine salt (DGL
salt).
Though Dicamba under normal application conditions provides good
selective control of weeds in monocotyledoneous crops, some times
when Dicamba is employed at very high dosage rates, e.g. when the
weed infection is severe, or unintentionally after wind drift, or
by overlapping of spray strips, loss in the treated crops may
occur.
One procedure to overcome the above indicated sensitivity responses
of plants to Dicamba involves varying the dosage rate. When a
reduction in the dosage rate is used to avoid phytotoxicity to the
crop plants, reduced weed control is often the result.
Another procedure involves changing the time of application or
modifying the ingredients used in the formulations containing the
active compound.
With Dicamba these methods have not always achieved the desired
result. Therefore there is still a need for a method of avoiding
the phytotoxic effects to crop plants.
Surprisingly, it has now been found that the co-application of a
quinolinyloxy alkanoic acid derivative and Dicamba at pre- or
post-emergence application results in a reduction of the phytotoxic
effects of the latter, particularly on grassy (monocotyledoneous)
crops such as maize, sorghum, turf, and cereals, without a
corresponding reduction of effectiveness in the control of
undesired weed plant growth.
This invention therefore concerns a method for reducing
phytotoxicity to crop plants due to Dicamba which comprises
co-applying to the crop or to the locus thereof Dicamba with a
phytotoxicity reducing amount of a quinolyloxy alkanoic acid
derivative.
Co-application can be achieved using tank mixes of preformulated
individual active ingredients, simultaneous or sequential
(preferably 1-2 days) application of such formulations or
application of preformulated fixed pre-mix combinations of the
individual active ingredients.
The application of the quinolinyloxy alkanoic acid derivatives may
also be used as an antagonistic seed treatment when pre- or
post-emergence spraying with Dicamba is intended. Such seed
treatment will be employed prior to planting of the seeds by
application of the quinolinyloxy alkanoic acid derivatives to the
locus of the seed, e.g. seed-furrow application, or by
seed-dressing according to the routine procedures. The application
of the active ingredients may be done to the surface of seeds, e.g.
by seed coating, or it may be done by spraying the locus of the
seed simultaneously at the time of sowing the crop area with the
seeds. The term seed is intended to embrace plant propagating
material such as seedlings, seeds, or germinated or soaked
seeds.
Quinolinyloxy alkanoic acid derivatives have been described in the
literature as herbicide safeners for different herbicides, in
particular for herbicidal phenoxyalkanoic acid derivatives,
sulfonyl-urea herbicides and chloroacetanilides. Inter alia EP-A-86
750, EP-A-94 349, EP-A-159 290, EPA-191736 and EP-A-492 366
disclose such active compounds, and their utility.
According to the present invention specially the quinolinyloxy
alkanoic acid derivatives of formula II ##STR2## wherein R.sub.1 is
hydrogen or halogen,
R.sub.2 is hydrogen or C.sub.1-4 alkyl, and
R.sub.3 is C.sub.1-12 alkyl, C.sub.1-6 alkoxy-C.sub.1-6 alkyl,
C.sub.3-6 alkenyloxy-C.sub.1-6 alky, or C.sub.3-6
alkinyloxy-C.sub.1-6 alkyl, have exhibited a remarkable capability
to reduce the phytotoxicity of Dicamba.
The preferred compounds of formula II are those wherein R.sub.1 is
halogen, preferably chlorine, R.sub.2 is hydrogen or methyl, and
R.sub.3 is C.sub.4-10 alkyl, preferably branched alkyl.
Examples for alkyl are methyl, ethyl, propyl, butyl, pentyl, hexyl,
heptyl, octyl, nonyl and decyl, including their isomeric forms.
Among C.sub.4-10 alkyl the branched alkyl groups are preferred.
Preferred examples of the branched alkyl are isopentyl,
2-ethylhexyl, 2-methylbutyl, 1,1 dimethylpropyl, 2-methylpropyl,
2-methylpentyl, 1-methylpentyl, tert.-butyl, 1-methylhexyl,
1-methylheptyl, 1-methyloctyl, 1-methylnonyl, 2-methylpentyl,
2-methylhexyl, 2-methylheptyl, 2-methyloctyl, 1,3-dimethylpentyl,
1,3-dimethylbutyl, 1,3-dimethylhexyl, and the like, with
1-methylhexyl being most preferred. Examples for alkoxyalkyl are
methoxyethyl, ethoxyethyl, or methoxylmethyl. Examples for
alkenyloxyalkyl
are allyloxyethyl, allyloxypropyl, methallyloxyethyl, or
2-butenyloxyethyl. Examples for aikinyloxy are propargyloxyethyl,
or propargyloxypropyl.
However, most preferred among the compounds of formula II is the
commercial compound Cloquintocet-mexyl (CGA 185 072), having the
chemical designation 1-methylhexyl
{(5-chloro-8-quinolinyl)oxy}acetate, hereafter designated as
compound IIa. Accordingly, the most preferred embodiments of
present invention comprise the method of controlling undesired
growth of weeds in monocotyledoneous crops by co-employing Dicamba
and Cloquintocet-mexyl, and a herbicidal composition comprising
Dicamba and Cloquintocet-mexyl as active ingredients.
The application rates of Dicamba and the quinolinyloxy alkanoic
acid derivative employed in co-application will of course depend on
the quinolinyloxy alkanoic acid derivative chosen, the weeds to be
controlled, the crop plant involved, soil type, season, climate,
soil ecology, and various other factors. Optimum usage is readily
determinable by one skilled in the art using routine testing such
as greenhouse or small plot testing. Application rates of Dicamba
will usually be those recommended for use of commercially available
forms of Dicamba.
In general, for example, satisfactory results are obtained when
co-applying at rates of 50 to 2000 g/ha, especially 100 to 1500
g/ha of Dicamba, and 10 to 2000 g/ha, especially 50 to 1500 g/ha of
a quinolinyloxy alkanoic acid derivative.
In general, for example, the weight ratio of Dicamba with a
quinolinyloxy alkanoic acid derivative lies conveniently within the
range of from 1:40 to 200:1, especially 1:15 to 30:1, e.g. 1:3,
1:1.2, 4:1, or 8:1.
A typical co-application of Dicamba (Compound I) with
Cloquintocet-mexyl (Compound IIa) would be e.g. from 250 to 1500
g/ha, especially 350 to 1200 g/ha of Compound I and 50 to 1500
g/ha, especially 100 to 1000 g/ha of Compound IIa.
The combinations of the invention are also surprisingly effective
when applied to the soil of the crop locus.
When applied to the soil, the quinolinyloxy alkanoic acid
derivatives are applied at a rate of 10 to 2000 g/ha, particularly
50 to 1500 g/ha. When applied as a seed dressing the compounds of
formula II are applied at a rate of 1.0 to 1000 g, particularly 5
to 800 g, e.g. 300 g, per 100 kg of seed. The amount of Dicamba
used as a spray on plants emerging from treated seeds are as given
above for co-application purposes.
With co-application of Dicamba and a compound of formula II it is
possible to control weeds in crops like cereals. Examples of such
weeds are:
______________________________________ Bayer Latin name English
name Code ______________________________________ Amaranthus species
Pigweed AMASS Anagalis arvensis Pimpernel, common ANGAR Bifora
radians BIFRA Brassica napus ssp. napus Oil seed rape BRSNN
Calystegia sepium Bindweed, hedge CAGSE Capsella bursa-pastoris
Shepherd's purse CAPBP Centaurea cyanus L. Knapweed CENCY Cerastium
arvense Chickweed, Field CERAR Chenopodium album Lambsquarters,
Common CHEAL Chenopodium polyspermum Goosefoot, Manyseeded CHEPO
Cirsium arvense Thistle, Canada CIRAR Convolvulus arvensis L.
Bindweed, Field CONAR Datura stramonium Jimsonweed DATST Fumaria
officinalis Fumitory, common FUMOF Galeopsis tetrahit L. Hempnettle
GAETE Galinsoga parviflora Smallflower GASPA Galium aparine
Cleaver, Bedstraw GALAP Helianthus annuus L. Sunflower HELAN Kochia
scoparia Kochia KOCSC Lapsana communis Nippelwort LAPCO
Lithospermum arvense L. Gromwell, field LITAR Matricaria chamomilla
Chamomile, wild MATCH Medicago sativa Alfalfa MEDSA Myosotis
arvensis Forgert-me-not, field MYOAR Papaver rhoeas Poppy, field
PAPRH Polygonum aviculare Knotweed, prostrate POLAV Polygonum
convolvulus Buckwheat, Wild POLCO Polygonum lapathifolium
Smartweed, Green POLLA Polygonum persicaria Ladystumb POLPE Primula
spp. Primrose PRISS Ranunculus arvensis Buttercup RANAR Rumex
obtusifolius.sup.1 Dock, Broadleaf RUMOB Salsola pestifer Thistle,
Russian SASKR Scandix pacten-veneris L. Venus comb SCAPV Senecio
vulgaris Groundsel, common SENVU Silene spp. Catchfly SILSS Sinapis
arvensis Mustard, Wild SINAR Sisymbrium officinale Mustard, hedge
SSYOF Solanum nigrum Nightshade, black SOLNI Solanum sarrachoides
Nightshade, hairy SOLSA Sonchus arvensis Sowthistle, Perennial
SONAR Sonchus oleracea Sowthistle, Annual SONOL Spergula arvensis
Spurry, corn SPRAR Stellaria media Chickweed, Common STEME
Taraxacum officinalis Dandelion, Common TAROF Thlaspi arvense
Pennycress, Field (Fanweed, THLAR Frenchweed, Stinkweed) Trifolium
repens Clover, white TRFRE Veronica arvensis Speedwell, corn VERAR
Veronica hederaefolia Speedwell, Ivyleaf VERHE Veronica persica
Speedwell, birdeye VERPE Vicia sp. Vetch VICSS
______________________________________
Co-applied active ingredients when formulated individually or used
as preformulated fixed pre-mixes are conveniently employed in
association with agriculturally acceptable diluents or
carriers.
The advantageous reduction of phytotoxicity is also observed in
certain cases where additional herbicidally active ingredients are
applied with the mixture of compounds I and II, and even also in
cases of synergistic mixtures of Dicamba with other herbicides.
It has now surprisingly been found that biologically active
semicarbazone compounds of formula III ##STR3## wherein
M is hydrogen, or a salt forming moiety like an alkali metal cation
or an optionally substituted ammonium e.g. isopropylammonium, and X
and Y represent independent hydrogen, fluorine or chlorine, which
form synergistic herbicidal combinations with Dicamba may be
employed in the method of the present invention.
A preferred compound of formula III are those wherein M is
hydrogen, potassium or sodium, and X and Y are fluorine. For this
carboxylic acid and its salts the common name Diflufenzopyr has
been proposed. For the purpose of this application Diflufenzopyr
will be referred to as Compound IIIa.
The additional component of formula III may be applied together
with the components I and II, either in a tank-mix preparation, or
as separate sprays, or in a ready-mix formulation which comprises
at least one of each components of formulae I, II and III. The
weight ratio of component I to component III may vary from 1:100 to
1000:1, preferably 1:10 to 100:1, especially 1:2 to 20:1, e.g. 1:1
to 10:1. Component III is applied at rates of 0.0010 to 1.1 kg/ha
preferably 0.010 to 0.55 kg/ha, especially 0.010 to 0.33 kg/ha.
The method applying component III, and three-way-mixtures
comprising active ingredients of formulae I, II and III also
represent aspects of the present invention.
The composition of the invention may be employed in any
conventional form, for example in the form of a twin pack, an
instant granulate, a flowable or a wettable powder in combination
with agriculturally acceptable adjuvants. Such compositions may be
produced in conventional manner, e.g. by mixing and grinding the
active ingredients with appropriate adjuvants (diluents and
optionally other formulating ingredients such as surfactants).
The term diluent as used herein means any liquid or solid
agriculturally acceptable material used to formulate a concentrated
material to a usable or desirable strength, including surfactants
and carriers, which may be added to the active constituents to
bring them in an easier or improved applicable form, respectively,
to a usable or desirable strength of activity. For dusts or
granules the diluent can be e.g. talc, kaolin or diatomaceous
earth, for liquid concentrate forms for example a hydrocarbon such
as xylene or an alcohol such as isopropanol, and for liquid
application forms e.g. diesel oil or preferably water.
Particularly formulations to be applied in sprayable forms such as
water dispersible concentrates or wettable powders may contain
surfactants such as wetting and dispersing agents. Surfactant as
used herein means an agriculturally acceptable material which
imparts emulsifiability, spreading, wetting, dispersibility or
other surface-modifying properties. Examples of surfactants are
lignin sulfonates, and fatty acid sulfonates, e.g. lauryl
sulfonate, the condensation product of formaldehyde with
naphthalene sulfonate, an alkylarylsulfonate, an ethoxylated
alkylphenol, an ethoxylated fatty alcohol and the like.
A seed dressing formulation is applied in a manner known per se to
the seeds employing the quinolinyloxy alkanoic acid derivatives and
a diluent in suitable seed dressing formulation form, e.g. as an
aqueous suspension or in a dry powder form having good adherence to
the seeds. Such seed dressing formulations are known in the art.
Seed dressing formulations may contain the quinolinyloxy alkanoic
acid derivatives in encapsulated form, e.g. as slow release
capsules or microcapsules.
In general, the formulations of combinations of Dicamba and the
quinolinyloxy alkanoic acid derivatives include from 0.01 to 90% by
weight of active agent(s), from 0 to 20% agriculturally acceptable
surfactant and 10 to 99.99% solid or liquid adjuvant(s), the active
agent(s) consisting of at least Dicamba together with a
quinolinyloxy alkanoic acid derivative. Concentrate forms of
compositions generally contain between about 2 and 80%, preferably
between about 5 and 70% by weight of active agent. Application
forms of formulation may for example contain from 0.01 to 20% by
weight, preferably from 0.01 to 5% by weight of active agent.
Useful formulations of the active ingredients either alone or in
combination include dusts, granules, suspension concentrates,
wettable powders, flowables and the like. They are obtained by
conventional manner, e.g. by mixing (an) active ingredient(s) each
optionally as twin packs with the diluent(s) and optionally with
other ingredients.
Alternatively, the active ingredients may be used in
microencapsulated form.
Agriculturally acceptable additives may be employed in the
herbicidal compositions to improve the performance of the active
ingredient and to reduce foaming, caking and corrosion, for
example.
For co-application for example as tank mixes or in sequential
treatment commercially available forms of the active ingredients
may be employed.
The compositions of the invention can also comprise other compounds
having biological activity, e.g. other compounds having a similar
or complementary herbicidal or antidotal activity or compounds
having fungicidal, insecticidal, or other pesticidal activity.
Solid forms for compositions are preferred from the point of view
of environmentally innocuous packaging.
The invention is illustrated by the following examples wherein
parts and percentages are by weight and temperatures are in
.degree. C.
EXAMPLE 1
Wettable Powder
60 parts of a mixture of Dicamba (DMA salt, 27.8%) and
Cloquintocet-mexyl (72.2%),
1 part sodium alkylnaphthalenesulfonate,
5 parts sodium alkylarylsulfonate-formaldehyde condensate,
5 parts highly disperse silica, and
29 parts kaolin
are ground until the particles have the desired size. A 60%
wettable powder containing 16.7% of Dicamba and 43.3% of
Cloquitocet-mexyl is obtained. The wettable powder is suitable for
spray purposes. It is applied as an aqueous suspension by an
apparatus suitable for the purpose.
EXAMPLE 2
Seed Dressing Formulation
25 parts of Cloquintocet-mexyl
15 parts of dialkylphenoxypoly(ethylenoxy)ethanol
15 parts of fine silica
44 parts of fine kaolin
0.5 parts of Rhodamine B as a colorant and
0.5 parts of Xanthan Gum
are mixed and ground in a contraplex mill at approx. 10'000 rpm to
an average particle size of below 20 microns. The resulting
formulation is applied to the seeds as an aqueous suspension in an
apparatus suitable for that purpose.
EXAMPLE 3
Seed Dressing Formulation
45 Parts of a Cloquintocet-mexyl are mixed with 1.5 parts of diamyl
phenoldecaglycolether ethylene oxide adduct, 2 parts of spindle
oil, 51 parts of fine talcum and 0.5 parts of colorant Rhodamin B.
The mixture is ground in a contraplex mill at 10'000 rpm until an
average particle size of less than 20 microns is obtained. The
resulting dry powder has good adherence and may be applied to
seeds, e.g. by mixing for 2 to 5 minutes in a slowly turning
vessel.
EXAMPLE 4
Granules
0.5 Parts by weight of a binder (a non-ionic tenside) are sprayed
onto 94.5 parts by weight of quartz sand in a tumbler mixer and
thoroughly mixed. 5 Parts by weight of a combination of compounds
of formulae I and IIa are then added and thorough mixing continued
to obtain a granulate formulation with a particle size in the range
from 0.3 to 0.7 mm.
EXAMPLE 5
Post-emergence Test
Active ingredient Compound I is used as aqueous spray prepared from
commercial BANVEL 480 SL (DMA-salt of Dicamba). Compound IIa is
employed as an aqueous spray prepared from a 10% emulsifiable
concentrate or dissolved in a (acetone/methanol/DMF/water,
45:4:1:50 by volume)-mixture (VE-mixture). Dilutions from these
stock solutions are performed to allow for preparation of spray
solutions consisting of single doses of individual or combined
active ingredients. Each dose is applied via a linear track sprayer
set to deliver 600 liters/ha spray volume to the foliage of the
selected crop/weed seedling species, postemergence application. The
seedlings used are cultured to develop plants at the two- to early
three-leaf stage. The average plant height at application time is
recorded. After application, the treated plants are transferred to
the greenhouse and held until termination of the experiment within
about three weeks. Plant height and symptoms of injury are recorded
twenty days after postemergence application, and the plant new
growth is determined as the difference between the plant height at
the end of the experiment and the plant height at the time of
treatment.
Co-application of Compound I with Compound IIa have been tested in
wheat (variety ZENITH), spraying first with the Compound IIa, and
after drying with compound I. In the tests the active ingredients
were applied to the tested plants alone and in combination with
each other. The obtained results were compared to the activity of
the herbicide when applied alone. The expected activities of the
combination is calculated from the results achieved by the single
active ingredients according to the method of Colby (Weeds 15,
1967, pages 20-22) utilizing the following calculation scheme for
two-component mixtures:
In this calculation method for the expected activity of a mixture E
is the expected activity of mixture comprising
Compound A at rate m
Compound B at rate n.
The results were as follows (expressed in % inhibition of the new
growth):
TABLE 1
__________________________________________________________________________
Compound I as BANVEL 480 SL Compound IIa as emulsifiable
concentrate 10% Assessment 20 days after treatment (% inhibition of
new growth) Wheat variety ZENITH Compound IIa g a.i./ha Compound I
30 100 300 1000 g a.i./ha 0 expected found expected found expected
found expected found
__________________________________________________________________________
0 0 0 0 0 0 384 31 31 7 31 15 31 30 31 28 768 67 67 67 67 54 67 53
67 52 1152 76 76 70 76 76 76 75 76 71
__________________________________________________________________________
TABLE 2
__________________________________________________________________________
Compound I as BANVEL 480 SL Compound IIa as VE-mixture Assessment
20 days after treatment (% inhibition of new growth) Wheat variety
ZENITH Compound IIa g a.i./ha Compound I 30 100 300 1000 g a.i./ha
0 expected found expected found expected found expected found
__________________________________________________________________________
0 0 0 0 0 0 384 31 31 34 31 39 31 24 31 2 768 67 67 78 67 75 67 55
67 54 1152 76 76 80 76 74 76 68 76 72
__________________________________________________________________________
EXAMPLE 6
Seed Treatment Test
Seeds of wheat (variety ZENITH) are coated with compound IIa using
an experimental seed treatment machinery (Hege 11). Rates per 100 g
of seeds are 0.1, 0.3 and 1.0 g a.i.
The treated seeds are planted into flower pots, covered with a
layer of soil, and sprayed with an aqueous solution of compound I
at rates of 144, 288 and 576 g a.i./ha. Each dose is applied via a
linear track sprayer set to deliver 600 liters/ha spray volume to
the surface of the planted pots. After application, the treated
plants are transferred to the greenhouse and held until termination
of the experiment within four weeks. Plant height and visual
ratings of plant injury symptoms are recorded twentyeight days
after application.
The visual rating of the plant injury and phytotoxicity symptoms is
done considering together mainly the plant leaning, the growth
inhibition and the plant deformation, and using the following
rating scale:
0: no injury/symptoms
1: weak injury/symptoms
2: moderate injury/symptoms
3: strong injury/symptoms
4: very strong injury/symptoms
The following results were obtained:
TABLE 3 ______________________________________ Plant injuring and
phytotoxicity symptoms Wheat (ZENITH) Assessment 28 days after
treatment (injury rating) Compound I Compound II (g a.i./100 g
seed) g a.i./ha 0 0.1 0.3 1.0
______________________________________ 0 0 0.05 0.17 0.13 144 2.29
0.78 0.96 0.88 288 3.21 1.50 1.13 1.46 576 3.43 1.83 2.95 2.83
______________________________________
TABLE 4 ______________________________________ Inhibition of plant
growth (% of check) Wheat (ZENITH) Assessment 28 days after
treatment Compound I Compound II (g a.i./100 g seed) g a.i./ha 0
0.1 0.3 1.0 ______________________________________ 0 0 -2 10 -4 144
47 8 2 -7 288 67 28 10 4 576 70 36 57 58
______________________________________
EXAMPLE 7
Field Tests
On standard field plots sown with spring wheat variety Stephens,
located in Idaho, USA (Trial I), the active ingredients Dicamba
(Compound I), Cloquintocet-mexyl (Compound IIa), and Diflufenzopyr
(Compound IIIa) are applied postemergence at the jointed stage of
the wheat with a conventional spray apparatus at usual spray volume
and at the given rates. Assessment of the injuring is done visually
51 days after treatment. In another trial with spring wheat variety
Penawawa, located in Oregon, USA (Trial II), the active ingredients
Dicamba (Compound I), Cloquintocet-mexyl (Compound IIa), and
Diflufenzopyr (Compound IIIa) are applied post-emergence at the
second node stage of the wheat with a conventional spray apparatus
at usual spray volume and at the given rates. The yield of the
harvested wheat crop is determined at the end of the growing
season, comparing treated and untreated plots.
The following results have been obtained.
______________________________________ Treatment application rate
damage in % yield in tons/ha Compound g/ha Trial I Trial II
______________________________________ Comp I 560 20 5.640 Comp IIa
100 2 6.200 Comp I+ 140+ 12 5.626 Comp IIIa 56 Comp I+ 560+ 2 6.321
Comp IIa 100 Comp I+ 140+ 2 6.753 Comp IIIa+ 56+ Comp IIa 100
untreated Control -- 0 6.753
______________________________________
* * * * *